Isoniazid

  • Isonicotinic acid hydrazide (INH )
  • Pyridine -4- carbohydrazide
  • J04AC01
  • J04AC51
  • J04AM02

Antibiotic

169-172 ° C

Moderately in water ( 125 g / l at 20 ° C)

Attention

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Isoniazid, also isonicotinic acid hydrazide, Eng. Isonicotinic hydracide acid, abbreviated INH, is a bactericidal antibiotic which is mainly applied in combination with rifampicin in the treatment of tuberculosis. HIV patients and prophylactic treatment with isoniazid may reduce the number of tuberculosis cases and the total deaths.

Isoniazid was synthesized in 1912 by Meyer and Malley at the University of Prague. Only after the Second World War, the antibiotic activity was detected. In the laboratories of Hoffmann -La Roche, Nutley, New Jersey Herbert H. Fox and employees isoniazid and iproniazid variant developed to market maturity. Gerhard Domagk also worked on these substances for Bayer AG.

In Mycobacterium tuberculosis, the tuberculosis bacterium, isoniazid by the enzyme catalase / peroxidase ( KatG ) is converted to isonicotinic acid radical, which anneals to the one NADH molecule, which is bound to the essential for the Mykolsäuresynthese reductase InhA, which thereby permanently is inhibited. Resistance, the newly developed the bacterium that relate exclusively to the katG gene and thus the activation of isoniazid.

When medication with INH can cause disorders of the central nervous system, gastro-intestinal disorders or allergies. Furthermore, intrahepatic jaundice may occur as a side effect. Pyridoxine (vitamin B6) may be added as Begleitpäparat to the side effects on the nervous system to reduce. In combination with alcohol, it can lead to a temporary intolerance to alcohol (chemical alcohol intolerance ).

INH is administered orally and usually it has a very good bioavailability ( ≈ 90%). In the liver it is acetylated to 75%. In addition, it is enzymatically hydrolyzed to isonicotinic acid. Isoniazid and its metabolites are excreted primarily by the kidneys.

Trade names

INH (A), Isozid (D), Rimifon (CH), Tebesium (D)

Iso - Eremfat (D), Isozid -comp. (D) Rifater (D, A, CH), Rifinab (D), Rifinah (CH), Rifoldin (A), Rimactazid (D), Rimstar (CH), Tebesium Duo / Trio ( D)

CAS registry number PubChem Anatomical Therapeutic Chemical Classification System DrugBank Dangerous Substances Directive (67/548/EEC) Hydrolysis Digital Object Identifier
419366
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